Document Type

Article

Publication Date

5-13-2026

Journal / Book Title

Beilstein Journal of Organic Chemistry

Abstract

A detailed experimental and computational study of the diastereoselectivity of cyclic sulfone synthesis by reaction of Rongalite with doubly electrophilic dienones is presented. Computational methods, including density functional theory, conformational search methods, and internal reaction coordinate methods, have been used to rationalize the diastereoselectivity of the reaction by transition-state modeling, and showcases the conformational subtleties of sulfur-containing rings. Extension of the original reaction to double intermolecular additions is also demonstrated along with a comparative study of Rongalite with the reactivity of other readily available sulfinate nucleophiles using competition and exchange experiments.

DOI

10.3762/bjoc.22.56

Rights

This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0).

Published Citation

Goga, M., Zong, H., Franco, J., Prana, J., Michel, R., Muro, A., Rubin, E., Brenya, J., Eshuis, H., & Bebbington, M. W. P. (2026). Rongalite addition to dienones: diastereoselectivity in cyclic sulfone synthesis; stereochemical rationalization and prospects as a general conjugate nucleophile. Beilstein journal of organic chemistry, 22, 742–752. https://doi.org/10.3762/bjoc.22.56

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